Production of Natural Fragrance Aromatic Acids by Coexpression of trans-Anethole Oxygenase and p‑Anisaldehyde Dehydrogenase Genes of Pseudomonas putida JYR‑1 in Escherichia coli
A gene encoding p-anisaldehyde dehydrogenase (PAADH), which catalyzes the oxidation of p-anisaldehyde to p-anisic acid, was identified to be clustered with the trans-anethole oxygenase (tao) gene in Pseudomonas putida JYR-1. Heterologously expressed PAADH in Escherichia coli catalyzed the oxidation...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2012-12, Vol.60 (48), p.11972-11979 |
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| container_issue | 48 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Han, Dongfei Kurusarttra, Somwang Ryu, Ji-Young Kanaly, Robert A Hur, Hor-Gil |
| description | A gene encoding p-anisaldehyde dehydrogenase (PAADH), which catalyzes the oxidation of p-anisaldehyde to p-anisic acid, was identified to be clustered with the trans-anethole oxygenase (tao) gene in Pseudomonas putida JYR-1. Heterologously expressed PAADH in Escherichia coli catalyzed the oxidation of vanillin, veratraldehyde, and piperonal to the corresponding aromatic acids vanillic acid, veratric acid, and piperonylic acid, respectively. Coexpression of trans-anethole oxygenase (TAO) and PAADH in E. coli also resulted in the successful transformation of trans-anethole, isoeugenol, O-methyl isoeugenol, and isosafrole to p-anisic acid, vanillic acid, veratric acid, and piperonylic acid, respectively, which are compounds found in plants as secondary metabolites. Because of the relaxed substrate specificity and high transformation rates by coexpressed TAO and PAADH in E. coli, the engineered strain has potential to be applied in the fragrance industry. |
| doi_str_mv | 10.1021/jf303531u |
| format | Article |
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Heterologously expressed PAADH in Escherichia coli catalyzed the oxidation of vanillin, veratraldehyde, and piperonal to the corresponding aromatic acids vanillic acid, veratric acid, and piperonylic acid, respectively. Coexpression of trans-anethole oxygenase (TAO) and PAADH in E. coli also resulted in the successful transformation of trans-anethole, isoeugenol, O-methyl isoeugenol, and isosafrole to p-anisic acid, vanillic acid, veratric acid, and piperonylic acid, respectively, which are compounds found in plants as secondary metabolites. Because of the relaxed substrate specificity and high transformation rates by coexpressed TAO and PAADH in E. coli, the engineered strain has potential to be applied in the fragrance industry.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf303531u</identifier><identifier>PMID: 23140548</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amino Acid Sequence ; Anisoles - metabolism ; Benzaldehydes - metabolism ; Benzoates - metabolism ; Biological and medical sciences ; Escherichia coli ; Escherichia coli - genetics ; Escherichia coli - metabolism ; Food industries ; Food microbiology ; Fundamental and applied biological sciences. Psychology ; genes ; Genetic Engineering - methods ; Hydroxybenzoate Ethers - metabolism ; Hydroxybenzoates - metabolism ; Molecular Sequence Data ; odors ; oxidation ; Oxidoreductases - genetics ; Oxidoreductases - metabolism ; Oxygenases - genetics ; Oxygenases - metabolism ; Pseudomonas putida ; Pseudomonas putida - genetics ; Pseudomonas putida - metabolism ; Recombinant Proteins - genetics ; Recombinant Proteins - metabolism ; Secondary Metabolism ; secondary metabolites ; substrate specificity ; vanillic acid ; Vanillic Acid - analogs & derivatives ; Vanillic Acid - metabolism</subject><ispartof>Journal of agricultural and food chemistry, 2012-12, Vol.60 (48), p.11972-11979</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a435t-29cdd6f099aa0dbaebc4c646e0acaeecdceb9f18ff045e83d3bf7c7a5a5f00883</citedby><cites>FETCH-LOGICAL-a435t-29cdd6f099aa0dbaebc4c646e0acaeecdceb9f18ff045e83d3bf7c7a5a5f00883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf303531u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf303531u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26721631$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23140548$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Han, Dongfei</creatorcontrib><creatorcontrib>Kurusarttra, Somwang</creatorcontrib><creatorcontrib>Ryu, Ji-Young</creatorcontrib><creatorcontrib>Kanaly, Robert A</creatorcontrib><creatorcontrib>Hur, Hor-Gil</creatorcontrib><title>Production of Natural Fragrance Aromatic Acids by Coexpression of trans-Anethole Oxygenase and p‑Anisaldehyde Dehydrogenase Genes of Pseudomonas putida JYR‑1 in Escherichia coli</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>A gene encoding p-anisaldehyde dehydrogenase (PAADH), which catalyzes the oxidation of p-anisaldehyde to p-anisic acid, was identified to be clustered with the trans-anethole oxygenase (tao) gene in Pseudomonas putida JYR-1. Heterologously expressed PAADH in Escherichia coli catalyzed the oxidation of vanillin, veratraldehyde, and piperonal to the corresponding aromatic acids vanillic acid, veratric acid, and piperonylic acid, respectively. Coexpression of trans-anethole oxygenase (TAO) and PAADH in E. coli also resulted in the successful transformation of trans-anethole, isoeugenol, O-methyl isoeugenol, and isosafrole to p-anisic acid, vanillic acid, veratric acid, and piperonylic acid, respectively, which are compounds found in plants as secondary metabolites. Because of the relaxed substrate specificity and high transformation rates by coexpressed TAO and PAADH in E. coli, the engineered strain has potential to be applied in the fragrance industry.</description><subject>Amino Acid Sequence</subject><subject>Anisoles - metabolism</subject><subject>Benzaldehydes - metabolism</subject><subject>Benzoates - metabolism</subject><subject>Biological and medical sciences</subject><subject>Escherichia coli</subject><subject>Escherichia coli - genetics</subject><subject>Escherichia coli - metabolism</subject><subject>Food industries</subject><subject>Food microbiology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>genes</subject><subject>Genetic Engineering - methods</subject><subject>Hydroxybenzoate Ethers - metabolism</subject><subject>Hydroxybenzoates - metabolism</subject><subject>Molecular Sequence Data</subject><subject>odors</subject><subject>oxidation</subject><subject>Oxidoreductases - genetics</subject><subject>Oxidoreductases - metabolism</subject><subject>Oxygenases - genetics</subject><subject>Oxygenases - metabolism</subject><subject>Pseudomonas putida</subject><subject>Pseudomonas putida - genetics</subject><subject>Pseudomonas putida - metabolism</subject><subject>Recombinant Proteins - genetics</subject><subject>Recombinant Proteins - metabolism</subject><subject>Secondary Metabolism</subject><subject>secondary metabolites</subject><subject>substrate specificity</subject><subject>vanillic acid</subject><subject>Vanillic Acid - analogs & derivatives</subject><subject>Vanillic Acid - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0U9u1DAUBnALgei0sOAC4A0SLAJ2HOfPMhraAqpoBXTBKnqxnzseJXGwE6mz6xU4DBfiJHg0od2wsmT_3ifrfYS84OwdZyl_vzWCCSn4_IisuExZIjkvH5MVi49JKXN-RI5D2DLGSlmwp-QoFTxjMitX5PeVd3pWk3UDdYZ-gWn20NEzDzceBoW09q6HySpaK6sDbXd07fB29BjCMjNFGJJ6wGnjOqSXt7sbHCAghUHT8c_dr3qwATqNm51G-mF_eLeQcxww7EOuAs7a9S7e0nGerAb6-cfXOMypHehpUBv0Vm0sUOU6-4w8MdAFfL6cJ-T67PT7-mNycXn-aV1fJJAJOSVppbTODasqAKZbwFZlKs9yZKAAUWmFbWV4aQzLJJZCi9YUqgAJ0sRdleKEvDnkjt79nDFMTW-Dwq6DAd0cGp6mIhNpwYtI3x6o8i4Ej6YZve3B7xrOmn1LzX1L0b5cYue2R30v_9USwesFQFDQmX0VNjy4vEh5Lnh0rw7OgGtiY9Fcf0tZTGGcV5JnD0mgQrN1sx_ivv7zpb9tcLVe</recordid><startdate>20121205</startdate><enddate>20121205</enddate><creator>Han, Dongfei</creator><creator>Kurusarttra, Somwang</creator><creator>Ryu, Ji-Young</creator><creator>Kanaly, Robert A</creator><creator>Hur, Hor-Gil</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20121205</creationdate><title>Production of Natural Fragrance Aromatic Acids by Coexpression of trans-Anethole Oxygenase and p‑Anisaldehyde Dehydrogenase Genes of Pseudomonas putida JYR‑1 in Escherichia coli</title><author>Han, Dongfei ; Kurusarttra, Somwang ; Ryu, Ji-Young ; Kanaly, Robert A ; Hur, Hor-Gil</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a435t-29cdd6f099aa0dbaebc4c646e0acaeecdceb9f18ff045e83d3bf7c7a5a5f00883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amino Acid Sequence</topic><topic>Anisoles - metabolism</topic><topic>Benzaldehydes - metabolism</topic><topic>Benzoates - metabolism</topic><topic>Biological and medical sciences</topic><topic>Escherichia coli</topic><topic>Escherichia coli - genetics</topic><topic>Escherichia coli - metabolism</topic><topic>Food industries</topic><topic>Food microbiology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>genes</topic><topic>Genetic Engineering - methods</topic><topic>Hydroxybenzoate Ethers - metabolism</topic><topic>Hydroxybenzoates - metabolism</topic><topic>Molecular Sequence Data</topic><topic>odors</topic><topic>oxidation</topic><topic>Oxidoreductases - genetics</topic><topic>Oxidoreductases - metabolism</topic><topic>Oxygenases - genetics</topic><topic>Oxygenases - metabolism</topic><topic>Pseudomonas putida</topic><topic>Pseudomonas putida - genetics</topic><topic>Pseudomonas putida - metabolism</topic><topic>Recombinant Proteins - genetics</topic><topic>Recombinant Proteins - metabolism</topic><topic>Secondary Metabolism</topic><topic>secondary metabolites</topic><topic>substrate specificity</topic><topic>vanillic acid</topic><topic>Vanillic Acid - analogs & derivatives</topic><topic>Vanillic Acid - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Dongfei</creatorcontrib><creatorcontrib>Kurusarttra, Somwang</creatorcontrib><creatorcontrib>Ryu, Ji-Young</creatorcontrib><creatorcontrib>Kanaly, Robert A</creatorcontrib><creatorcontrib>Hur, Hor-Gil</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Dongfei</au><au>Kurusarttra, Somwang</au><au>Ryu, Ji-Young</au><au>Kanaly, Robert A</au><au>Hur, Hor-Gil</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Production of Natural Fragrance Aromatic Acids by Coexpression of trans-Anethole Oxygenase and p‑Anisaldehyde Dehydrogenase Genes of Pseudomonas putida JYR‑1 in Escherichia coli</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2012-12-05</date><risdate>2012</risdate><volume>60</volume><issue>48</issue><spage>11972</spage><epage>11979</epage><pages>11972-11979</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>A gene encoding p-anisaldehyde dehydrogenase (PAADH), which catalyzes the oxidation of p-anisaldehyde to p-anisic acid, was identified to be clustered with the trans-anethole oxygenase (tao) gene in Pseudomonas putida JYR-1. Heterologously expressed PAADH in Escherichia coli catalyzed the oxidation of vanillin, veratraldehyde, and piperonal to the corresponding aromatic acids vanillic acid, veratric acid, and piperonylic acid, respectively. Coexpression of trans-anethole oxygenase (TAO) and PAADH in E. coli also resulted in the successful transformation of trans-anethole, isoeugenol, O-methyl isoeugenol, and isosafrole to p-anisic acid, vanillic acid, veratric acid, and piperonylic acid, respectively, which are compounds found in plants as secondary metabolites. Because of the relaxed substrate specificity and high transformation rates by coexpressed TAO and PAADH in E. coli, the engineered strain has potential to be applied in the fragrance industry.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>23140548</pmid><doi>10.1021/jf303531u</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2012-12, Vol.60 (48), p.11972-11979 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Amino Acid Sequence Anisoles - metabolism Benzaldehydes - metabolism Benzoates - metabolism Biological and medical sciences Escherichia coli Escherichia coli - genetics Escherichia coli - metabolism Food industries Food microbiology Fundamental and applied biological sciences. Psychology genes Genetic Engineering - methods Hydroxybenzoate Ethers - metabolism Hydroxybenzoates - metabolism Molecular Sequence Data odors oxidation Oxidoreductases - genetics Oxidoreductases - metabolism Oxygenases - genetics Oxygenases - metabolism Pseudomonas putida Pseudomonas putida - genetics Pseudomonas putida - metabolism Recombinant Proteins - genetics Recombinant Proteins - metabolism Secondary Metabolism secondary metabolites substrate specificity vanillic acid Vanillic Acid - analogs & derivatives Vanillic Acid - metabolism |
| title | Production of Natural Fragrance Aromatic Acids by Coexpression of trans-Anethole Oxygenase and p‑Anisaldehyde Dehydrogenase Genes of Pseudomonas putida JYR‑1 in Escherichia coli |
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